After graduating from Bishop George Ahr High School, Darrin Winston attended Rutgers University. As a senior there in 1988, he won 10 games and struck out 73, and overall, he holds the Rutgers career records with 38 starts, 26 wins, and 22 complete games.

Winston was selected by the Montreal Expos in the 18th round of the 1988 amateur draft. He worked his way through the minor league ranks, missing the entire 1992 campaign due to Tommy John surgery, and was out of pro ball for the entire 1996 campaign. After being signed by the Philadelphia Phillies in 1997, he made his big league debut as 31 year old as a September call-up. He appeared in 27 games out of the bullpen for the Phillies the next year.